Pyloricidin B
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| Category | Antibiotics |
| Catalog number | BBF-02082 |
| CAS | |
| Molecular Weight | 554.63 |
| Molecular Formula | C26H42N4O9 |
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Description
Pyloricidin B is an antibiotic against Helicobacter pylori produced by Bacillus sp. HC-70. It has strong anti-Helicobacter pylori activity, with a MIC of 0.0625 pig/mL. It has no activity against other bacteria and yeast.
Specification
| IUPAC Name | (3R)-3-[[(2R,3S,4S,5R)-5-[[(2S)-2-[[(2S)-2-amino-3-methylbutanoyl]amino]-4-methylpentanoyl]amino]-2,3,4,6-tetrahydroxyhexanoyl]amino]-3-phenylpropanoic acid |
| Canonical SMILES | CC(C)CC(C(=O)NC(CO)C(C(C(C(=O)NC(CC(=O)O)C1=CC=CC=C1)O)O)O)NC(=O)C(C(C)C)N |
| InChI | InChI=1S/C26H42N4O9/c1-13(2)10-17(29-25(38)20(27)14(3)4)24(37)30-18(12-31)21(34)22(35)23(36)26(39)28-16(11-19(32)33)15-8-6-5-7-9-15/h5-9,13-14,16-18,20-23,31,34-36H,10-12,27H2,1-4H3,(H,28,39)(H,29,38)(H,30,37)(H,32,33)/t16-,17+,18-,20+,21+,22+,23-/m1/s1 |
| InChI Key | RQPIUFLNFUDVAY-CRTOORPBSA-N |
Properties
| Appearance | Colorless Needle Crystal |
| Antibiotic Activity Spectrum | Gram-negative bacteria |
| Boiling Point | 982.6±65.0°C at 760 mmHg |
| Density | 1.3±0.1 g/cm3 |
Reference Reading
1. Synthesis and anti-Helicobacter pylori activity of pyloricidin derivatives I. Structure-activity relationships on the terminal peptidic moiety
Atsushi Hasuoka, Yuji Nishikimi, Yutaka Nakayama, Keiji Kamiyama, Masafumi Nakao, Ken-ichiro Miyagawa, Osamu Nishimura, Masahiko Fujino J Antibiot (Tokyo). 2002 Mar;55(3):322-36. doi: 10.7164/antibiotics.55.322.
The novel natural antibiotics pyloricidin A, B and C possess potent and highly selective antibacterial activity against Helicobacter pylori. In order to investigate the structure activity relationships for the terminal peptidic moiety, a series of pyloricidin B and pyloricidin C derivatives, bearing various amino acids in the moiety, were prepared and evaluated for their anti-H. pylori activity. The derivatives bearing alpha-D-, beta- and gamma-amino acids or peptidemimetics showed drastically decreased activity. On the other hand, the derivatives with a-L-amino acids were found to maintain the activity. Among the derivatives prepared in this work, the allylglycine derivative 2s showed the most potent anti-H. pylori activity, with an MIC value of less than 0.006 microg/ml against H. pylori NCTC11637, which is 60-fold greater than the activity of the lead compound pyloricidin C.
2. Pyloricidins, novel anti-helicobacterpylori antibiotics produced by Bacillus sp. I. Taxonomy, fermentation and biological activity
M Nakao, K Miyagaw, Y Nakano, T Sakane, M Tada, O Nishimura, M Fujino J Antibiot (Tokyo). 2001 Nov;54(11):926-33. doi: 10.7164/antibiotics.54.926.
Novel anti-Helicobacter pylori antibiotics, pyloricidins A, A1, A2, B, C and D, were discovered in the culture broth of two bacilli strains. Pyloricidins selectively inhibited the growth of H. pylori. Pyloricidin B was efficacious in the treatment of gastric infection caused by H. pylori in Mongolian gerbils and may be promising for cure of H. pylori infection as a single agent.
3. Synthesis and anti-Helicobacter pylori activity of pyloricidin derivatives II. The combination of amino acid residues in the dipeptidic moiety and its effect on the anti-Helicobacter pylori activity
Atsushi Hasuoka, Yuji Nishikimi, Yutaka Nakayama, Keiji Kamiyama, Masafumi Nakao, Ken-ichiro Miyagawa, Osamu Nishimura, Masahiko Fujino J Antibiot (Tokyo). 2002 May;55(5):499-507. doi: 10.7164/antibiotics.55.499.
The novel natural antibiotics pyloricidin A, B and C, consisting of a common (2S,3R,4R,5S)-5-amino-2,3,4,6-tetrahydroxyhexanoyl-beta-D-phenylalanine moiety and a terminal peptidic moiety (pyloricidin A: L-valine-L-valine-L-leucine; pyloricidin B: L-valine-L-leucine; pyloricidin C: L-leucine), exhibit potent and highly selective anti-Helicobacter pylori activity. In order to develop more potent compounds and to investigate structure activity relationships for the peptidic moiety with regard to the combination of amino acids, a series of derivatives with various dipeptidic moieties were prepared and evaluated for their anti-H. pylori activity. The combination of the two amino acids in the moiety was found to have a significant effect on the activity; the compound with Nva-Abu showed excellent anti-H. pylori activity with an MIC value of 0.013 microg/ml against H. pylori TN2. In addition, this compound was found to show 60% clearance of H. pylori from infected Mongolian gerbils upon repetitive oral administration (10 mg/kg, b. i. d. for 7 days).
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
